6-trimethylsilylhex-5-yn-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 gm of 6-trimethylsilylhex-5-ynol in 400 ml of dry dimethylformamide, was added 98 gm of pyridinium dichromate. The solution was stirred in the dark for 24 hours and then partitioned between ether and water. The ether extract was dried over magnesium sulphate and evaporated to an oil. Distillation gave the title compound, b.p. 121°-124° C. (1 mm Hg), IR: 3290, 2162, 1720 cm-1. partitioned between ether and water The ether extract was dried over magnesium sulphate evaporated to an oil Distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 gm of 6-trimethylsilylhex-5-ynol in 400 ml of dry dimethylformamide, was added 98 gm of pyridinium dichromate. The solution was stirred in the dark for 24 hours and then partitioned between ether and water. The ether extract was dried over magnesium sulphate and evaporated to an oil. Distillation gave the title compound, b.p. 121°-124° C. (1 mm Hg), IR: 3290, 2162, 1720 cm-1. partitioned between ether and water The ether extract was dried over magnesium sulphate evaporated to an oil Distillation

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-trimethylsilyl(hex-1-yn-6-ol) (32.6 g, 190 mmol) and pyridine (0.38 mL) dissolved in diethyl ether (100 mL) was added slowly phosphorus tribromide (7.1 mL, 75 mmol) in diethyl ether (20 mL). Upon addition a precipitate formed and the heterogeneous solution was stirred at room temperature overnight. The mixture was then heated at reflux for 2.5 hours and, upon cooling, was poured onto ice, washed with water, sodium bicarbonate solution, brine and dried (MgSO4). Evaporation of solvent under reduced pressure gave a residue which was distilled (b.p. 80° C., 3.5 mm Hg) to give 22 g (50%) of product. 1H NMR (CDCl3) δ: 0.14 (s, 9H), 1.64-1.72 (quintet, 2H), 1.91-2.02 (quintet, 2H), 2.27 (t, 2H), 3.44 (t, 2H) ppm. Upon addition a precipitate formed The mixture was then heated at reflux for 2.5 hours upon cooling was poured onto ice washed with water, sodium bicarbonate solution, brine dried (MgSO4) Evaporation of solvent under reduced pressure gave a residue which was distilled (b.p. 80° C., 3.5 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-trimethylsilyl(hex-1-yn-6-ol) (32.6 g, 190 mmol) and pyridine (0.38 mL) dissolved in diethyl ether (100 mL) was added slowly phosphorus tribromide (7.1 mL, 75 mmol) in diethyl ether (20 mL). Upon addition a precipitate formed and the heterogeneous solution was stirred at room temperature overnight. The mixture was then heated at reflux for 2.5 hours and, upon cooling, was poured onto ice, washed with water, sodium bicarbonate solution, brine and dried (MgSO4). Evaporation of solvent under reduced pressure gave a residue which was distilled (b.p. 80° C., 3.5 mm Hg) to give 22 g (50%) of product. 1H NMR (CDCl3) δ: 0.14 (s, 9H), 1.64-1.72 (quintet, 2H), 1.91-2.02 (quintet, 2H), 2.27 (t, 2H), 3.44 (t, 2H) ppm. Upon addition a precipitate formed The mixture was then heated at reflux for 2.5 hours upon cooling was poured onto ice washed with water, sodium bicarbonate solution, brine dried (MgSO4) Evaporation of solvent under reduced pressure gave a residue which was distilled (b.p. 80° C., 3.5 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Trimethylsilyl[6-(oxacyclohex-2-yloxy)]hex-1-yne (76 g, 300 mmol) and pyridinium p-toluenesulfonate (0.05 g) were heated at reflux in methanol (200 mL). After cooling the solvent was removed under reduced pressure, the residue was dissolved in methylene chloride and washed with water, brine and dried (MgSO4). Evaporation of the solvent under reduced pressure afforded a residue which was distilled (b.p. 96° C., 3 mm Hg) to give 37.6 g (64%) of the product. After cooling the solvent was removed under reduced pressure the residue was dissolved in methylene chloride washed with water, brine dried (MgSO4) Evaporation of the solvent under reduced pressure afforded a residue which was distilled (b.p. 96° C., 3 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 gm of 6-trimethylsilylhex-5-ynol in 400 ml of dry dimethylformamide, was added 98 gm of pyridinium dichromate. The solution was stirred in the dark for 24 hours and then partitioned between ether and water. The ether extract was dried over magnesium sulphate and evaporated to an oil. Distillation gave the title compound, b.p. 121°-124° C. (1 mm Hg), IR: 3290, 2162, 1720 cm-1. partitioned between ether and water The ether extract was dried over magnesium sulphate evaporated to an oil Distillation